1,1'-Carbonyldiimidazole → Ethyl 3-(7-fluoro-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxalin-1-yl)propanoate

HRID 72742Notes

Reaction equation

HRID 72742 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>ClC1C=CC=CC=1Cl>[F:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[N:9]1[C:10]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:11][CH:12]=[C:13]1[C:21](=[O:22])[NH:1]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59198670Ethyl 3-[1-(2-amino-4-fluorophenyl)-1H-imidazol-2-yl]-propanoate

Product 1

HCID 59198645Ethyl 3-(7-fluoro-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxalin-1-yl)propanoate

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

Ethyl 3-[1-(2-amino-4-fluorophenyl)-1H-imidazol-2-yl]-propanoate as synthesized in Production Example 92, 94 mg, 1,1′-carbonyldiimidazole 83 mg and 1,2-dichlorobenzene 1 mL were mixed and heated under reflux for 0.5 hour. Further 1 mL of 1,2-dichlorobenzene was added and the heating under reflux was continued for further 3 hours. Allowing the reaction liquid to cool off, the precipitate was recovered by filtration, and washed with diethyl ether and ethyl acetate, by the order stated. The resulting crystals were dissolved in a liquid mixture of tetrahydrofuran and methanol, and the insoluble matter was separated by filtration. Distilling the solvent off under reduced pressure, 70 mg of the title compound was obtained.

Workup

  1. additionwere mixed
  2. temperatureheated
  3. temperatureunder reflux for 0.5 hour
  4. temperaturethe heating under reflux
  5. customAllowing the reaction liquid
  6. temperatureto cool off
  7. filtrationthe precipitate was recovered by filtration
  8. washwashed with diethyl ether and ethyl acetate, by the order
  9. dissolutionThe resulting crystals were dissolved in a liquid mixture of tetrahydrofuran and methanol
  10. customthe insoluble matter was separated by filtration
  11. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-5c8fa01212dc49f4b024a0aba7fcc5b7
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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